One Quickie

Breaking on exceptions (gdb->General)
It can be annoying tracking down the cause of thrown exceptions in Cocoa. you get a notice like 2007-05-05 17:18:00.702 QueenStitcher[2804:117] *** Assertion failure in -[NSColorWell setColor:], NSColorWell.m:497, u suk l0s3r, and then the runloop happily runs again, giving you no clue where the problem is. I tell gdb to always break on Cocoa exceptions:
fb -[NSException raise]
fb objc_exception_throw()
For maximal enjoyment, add these two lines to your ~/.gdbinit file, so they'll get set no matter how you invoke gdb (no need to add these to every single project, for instance).

I've been told VoiceOver uses exceptions heavily, so if you're doing VoiceOver development, these breaks may cause you pain.

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